


All Business And Rivalry

by bangtasticbobby



Category: Supernatural
Genre: F/M
Language: English
Status: In-Progress
Published: 2019-01-17
Updated: 2019-05-01
Packaged: 2019-10-11 17:18:37
Rating: Not Rated
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 17
Words: 14,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17451104
Author URL: https://archiveofourown.org/users/bangtasticbobby/pseuds/bangtasticbobby
Summary: There's a dispute between brothers, but on what account? Was it the woman that tried desperately to keep them together? She would only hope against that, not only does she doubt herself- her guilt, but the trust between her and her connections. Can she never catch a break?





	1. Chapter 1

**Author's Note:**

> Hi! I'm new but I'm alot let new on Tumblr and wattoad at bangtasticbobby so you can catch me there too, anyways enjoy the first chapter to ABAR feed back is cool! And I take requests! Okay okay bye.

The confident women walked the halls of the janky strip club, knowing exactly where she was headed. Past the guards at the last door, and right in front of the tailored man talking to a couple of goons who looked like they had no idea what was happening. This place was run so differently than the one she'd previously been too. 

"Welcome, Y/n." The two 'gangsters' gazed back as the voice spoke of her presence. They looked nervous as a man had walked in behind her, dark energy looming. The trench coat was a dead give away, she could practice taste the fear in their eyes. So ignoring who had addressed her, she leaned into the darker skinned male. He was very small compared to the other. "Yes, not at all the myth you've learned hmm?" Y/n stood straight once more scanning her eyes down the front of her companion and smirked. "He's larger than in the stories." 

There was a fifth of silence shoved down the poor boys throat as he gazed into the eyes of the trench coat man. "Castiel. If you would escort these pathetic men out of here," She paused to lay a hand on his chest. "It would be very much appreciated." 

She took one of their seats as he dragged them by their shirts, the chair was still warm and she lightly ran her fingers through her hair. "Hello, Dean." He didn't take his eyes off of her, it'd be dangerous too. "I come baring news." She scoffed as his posture changed from interested to the opposite. "It's about-" He cut her off as he stood, rounded the large oak desk and leaned atop, just aside her.

"I know what its about." There was a sickly sweet smile that fell from her lips, twisting things in his gut like no other. "Well then, what's the proposal?" He watched her curl her feet up on the chair, shoes already disposed of and comfort lacing her actions. She wasnt afraid of him by any means and that twisted something different inside of him.

"He can find himself a new garden, I've been using that lot for three years!" He had turned to kick at the desk. "Listen Dean-" With a sharp look she closed her mouth with a scowl. "Mr. Winchester, listen to me very carefully. It wouldn't be very wise to walk the path your trying to." She looked at the worn floor, the carpet was torn a bit just under the desk foot. "He has twice the men and weaponry," She stopped for a moment letting a smirk fall into place and tilted her head a tiny bit to look up at Dean. "Tripple the brain." 

His hand came around her neck quickly, bringing her closer. "I'd watch your fucking mouth if I were you." Then he dropped her and she chuckled. "Like father like son, huh?" She let her words soak in while she rubbed her neck "Although am I wrong, Dean? He does." 

She exclaimed his name in such a sugary manner, and he looked indecisive. "I've been in the business longer than him," A grimace crawling up his features. "You just go tell Sammy he's in for one hell of a ride." She shrugged at his speech, quickly sliding her shoes on once more. "I'd love too, but he's said the same."  Her hand touched the door knob before it was opened for her. "Thank you Castiel." 

He dipped his head in response. "And Dean, don't put your hands on me again or I can promise you," She turned to face him, Castiel now stood straight protectively. "One hell of a fucking ride." She fixed the neck of her sweater and walked the halls once more, waiting as Castiel closed the door politely. 

As soon as they were out of the club and in their car, she turned away from her partner. "Underneath his desk," Her eyes following the passing houses. "I'm willing to bet there's something there." Her sharp intake of air startled the man in the drivers seat as she dismissed the thought, "But put it on the to-do list Cas, let's have a night of drinking."


	2. Chapter 2

The next day she didn't look like a dead man walking, her posture was straight and she had on her favorite gown. For today she met with and old buddy. Nothing she could do or say would make Sam back down, but she continued her job. "Y/n, why do we do this anyways?" Asked her 'guardian angle'. She didn't answer. 

"I don't know what I'd do without Sammy, Y/n." His voice echoed in her head and she snapped back to reality. "For reasons that will stay unknown to you Castiel." He huffed, interrupting her, "Let me finish, Angel." She composed herself, took a deep breath and attempted to get an intelligent answer out. "Y-You wouldn't understand." The odds weren't in her favor this time. Again the houses out of the window caught her interest. They seemed so well put together and perfect, it made her angry. 

"I'm sure they wouldn't understand if it was brought to their attention either, so don't feel left out old friend." As she spoke they made it to their destination. It was a mansion of sort, filled with men guarding doors. You'd been here before you knew the drill. "I'm Y/n L/n. I'm here to see Samuel, on business terms." She smiled sarcastically at the guard who looked her up and down. 

"Business huh?" He snickered and threw an elbow at his partner. Castiel made a displeased sound from behind her and the men took notice of how tense the trench coated man was. She rose her hand and Castiel relaxed. "I'm sorry, but innappropriate jokes in the work place? I'm gonna have to call HR." She laughed cutely. "No but that was a good one..." Her smiled faded, "For someone with and IQ of three, really? I thought Sammy was teaching you goons here?" 

She did a snarky lip curl, "Or are those privileges only for the field workers?" A buzzer sounded and the men jumped, watching as Y/n adjusted her outfit and waited for the speaker to give it's announcement. "Let her through." A sharp tone for Sammy. She smiled, she must've gotten to him. As they made it up the stairs to Sam's office she heard Castiels voice in her ear. "Are we sure this is a good idea, it's not too late to-" She stopped his speech by opening the door to the white office.

"Hello Sammy!" Again she barged into a meeting of some sort but this time it looked like a 'sit-around-the table-and-discuss things-meeting'. She had to admit, Dean asserted his dominance in a very different way. "Y/n, if you wouldn't mind sitting and waiting for me to finish. I'm sure this is more important than our little chats." 

She hummed, clearly angry at what had just been said. Even more so after the other, maybe seven, men laughed along his chuckles. "Actually Samantha, it's about squirrel. I think that's of some importance? He's got such plans boss-" She shook her head, at his displeased grunt. She needed something to finish the meeting. She thought for a moment before she smirked and walked behind Sam's chair. Her hands ran down his chest and she could feel the way he pushed into it. 

She didn't say anything yet, letting all the little mice before her watch as this man crumbled at her touch. He continued with his meeting as she moved around him, finally making it to his lap. She ground down and he held her hips, "Y/n/n," He said in a warning tone, his word almost of a moan, he was getting worked up. As was another of the members in the room but in a negative way. "You see the one in the red leather?" She pointed to the one getting angry at how Samuel was acting with her.

He nodded, trying hard not to buck his hips and loose his composure in front of his minions. "He's a rat from Dean's side. Found out yesterday." She whispered sultry in his ears and he snapped stopping the conversation between the seven men before them. "Take him to the back, he's a mole." The man's eyes doubled in size and he pleaded otherwise. He lifted her up on the table as the men cleared out. The white tuxedo was almost to Bright for her eyes as he smirked "Now that you've got my attention..."


	3. Chapter 3

Effectively the meeting had been ended and Sam's lips were on her neck. She rolled her eyes to the back of her head trying to enjoy the moment while it lasted. Eventually she attempted to move away from him and from her place on the table. Sam made a displease growl, yet she struggled more his hands holding her firm in her place and she struggled to get him off of her.

"Sam- Stop." He pushed her off angrily, her falling back on her hands, the table shaking afterwards. "I guess reminding ourselves of old times conjures up a lot of loose, torn ends." You shoo'ed Castiel away from your side and Samuel laughed, making note of the puppy dogs attitude. He was so attached to her.  
"Anyways-" He said as he was rounding his desk, and sitting himself onto his seat. "What are these big plans Dean has." Y/n cleared her throat. "He's gonna fight til one of you drop. I advise you-" His amused hums interrupted her rudely. "Yes you always have the advice don't you." Another memory flashed through her head. "Really? Should I wait for Dean?" Again he cut your thought process off. "Yes, your advice worked so well all those years ago."

She rose her lips in anger. "Take it or don't I'm simply the message man, shoot me if you want but-" She put her hands up deciding not to finish her sentence. The look on Sam's face gave her an idea of who he'd be shooting, when Castiel came to stand between you. "Can your dog leave the room for one second?!" He had a possessive look for some reason.

You dismissed Castiel as you stood like stone to Samuels rage. As he left you continued to conversate. "Your a big boy now Samuel, so don't take my advice." She just didn't want them to tear each other apart.

"It's amazing though-" She sat in a chair around the white table. She didn't know what else to say. "How much I've learned from your father." Her fingers clasped together and she saw his back straighten. "Father taught you?" She 'ahh'ed' "Yes, I was like-" Y/n pondered on it for a minute. "I guess I couldn't say I was like a daughter, we had some other relations that proved that title a little wrong." His frown was evident once more.

"What's your advice?" She smiled lightly at his question, her intentions weren't vicious or hurtful. "Leave the gravesite alone and find another dump, you know how your brother is. He wont-" He finished her sentence. "You have no idea what this rivalry is over do you?"

She pondered it and listened as he spoke once more. "But I know what I'm doing. I've been in the game long enough and I wasn't raised like an obedient lap dog." He fixed his tie and stood, missing your offended face. "I've also got a few tricks up my sleeve." Her gown fell around her form as she stood with him. "Well I'll be sure to let him know-"

Her dull eyes met his again and her eyebrows creased in concern. "Just- Just be smart." Her face hardened and she walked to the limo that brought her there. She found Castiel on the way out. "I fear there's going to be a battle that I can't stop this time."

_"Y/n/n! Look at this slug, Dean told me to put it in your shirt but I said no way!" She snickered and took it from him placing it on the branch of the tree she sat under. "Damn it Sammy, your not supposed to tell her the plan." The younger of the three shushed the boys, "Shush your father might know we're out late." Dean rolled his eyes at her responsible personality._

_"You didn't have to come princess." She shook her head sternly, "I'll always help you do what you want, protect you. That's why I'm here, if you father happens to catch us I will be the blame. I could never watch you two get hurt." Their faces softened, "Y/n, were supposed to do that for you." Sam is the one that said it, for Dean had tears at the corners of his eyes. He was always a sensitive boy, "You guys don't understand. I have to." She paused, closing the journal she was drawing in. "It's my job."_


	4. Chapter 4

_MARCH 20TH 2003_

"Y/n, we can _leave_. Finally _we can leave._ " He was almost to tears trying to explain to her. "I finally got the Impala, now all we gotta do is book a flight outta here." Dean was getting frustrated at the little 19 year old. "Dean I can't just leave here, my mother." Dean angrily threw the marker in his hand, hitting and marking a wall. "Your mother is about as abusive as your step father."

She sighed. "John, isn't-" She couldn't finish her sentence, the boys didn't know and she wasn't supposed to tell. He was sweet, he just had to have a front. A front for the world. So she _tried_ to believe. "He isn't what?!" He was whisper yelling, almost red in the face. "He's not like that with me!" She said with the same tone level.

"Oh, so your just _so_ special?" Her eyebrows furrowed in anger. "You know my opinions on who comes first and who's the most important." She spoke sternly. "Im just a pawn in the game, I'm the minor character- plus you really think he won't go lookin' after us?" She chuckled a bit. "You guys are supposed to be the big badass heros who save the world from criminals," she sat silent for a moment "criminals like your father. I- I would only slow ya' down."

John Winchester _was_ a criminal, a nasty man, she had to remind herself that. He killed many men and women, and not to mention the four year relationship he had with his step daughter. "Listen your gonna make it out of here, Y/n/n." He stuttered, looking determined. "B-Because if-if you don't I'll dig my ass down to hell and drag you up my-fucking-self." She laughed loudly, the action was impossible but the thought was nice.

"Me and Sammy, we were gonna leave together. Drag you along too." His jaw ticked. "Yet he left, and I'm not gonna do the same to you. I'm not gonna leave you behind." Dean dropped his head in his hands and leaned against the head board of her bed. "Dean-" She called out his name so softly, so caring. She just needed to do something. And when he turned and she leaned in, he couldn't help it. Her soft lips had caught his and in the first time in forever he felt heaven.

Things escalated and he quickly pulled the girl to his lap. "Are you sure?" He asked and she smiled so wide with appreciation. It caught her off guard. No one's ever asked her. "Yeah, it'll get both our minds off things." She rubbed her hands up and under his shirt, then raked her nails down again, grinding against him. He gasped. _Like father like son_. She faltered at her thought. "Is-Is this your first time?"

He was so eager to hear her say 'yes'. She could see it in his eyes he'd wanted to have her like this, like that, for a while. "Yeah." She lied. "Show me how?" The teenager ran her hands threw his hair and he sat up a bit more.

"First we-we take your shirt off." He took the hem of her t-shirt and looked up into her eyes. She nodded lifting her hands above her head. When the white cloth was out of the way he breathed a deep sigh and took in her form, running hands along her hips and her front- anywhere he could touch.

She whined, "Dean." She didn't know why she said his name, but it felt good rolling off her tongue. This was so slow paced compared to her last encounters. So different. "Yeah sweetheart I, im-" He paused reaching around to unbuckle her bra. "I'm going- I want us to savor this." She discarded the rest of her clothing then helped the 24 year old with his. Kissing up his chest every chance she got and finally after the flannel was removed she kissed and bit on his neck.

He groaned, hands gripping tightly to her hips. "For being step siblings this is a little _naughty_." The hand on his chest could feel the way his heart raced after the comment. "God- But you like it don't you?" He spoke into the shell of her ear. "I wonder what else you'd let me do." He lifted them up to shimmy his pants down only to rest himself bare against her stomach and thigh when he was done.

Her hand found way to his tip and she worked magic on him like nothing. Almost like she'd perfected the movements. His nails made cresents on her smooth skin and he bucked into her palm. She moved the thin silk of her underwear to the side, instead of troubling herself to take them off. He groaned at her eagerness and watched as she eased him into herself.

What a sight for him to see, what a feeling to feel, and if they'd known the angry eyes watching them they would've stopped right then and there for fear of death, but they were oblivious to the danger. _Oblivious_.

**Notes for the Chapter:**

> I have lots of love for this series and whatnot I really hope throughout the chapters that you do too!!  
> Feedback is great too, so I know anyways chapter 5 soon!!!


	5. Chapter 5

_MARCH, 24TH 2003_

The halls were quiet enough as she took her sketch books back to her room from spending time in the garden. Y/n's escape from everything was drawing, her main topic today was Dean. Usually it was always something morbid. She was glad it wasn't today.

As she passed John's study she heard the door knob creak open, he stood in the door way. He gave her that look he always did and she knew to drop what she had and follow him into that office of his. When she followed him she heard his strained voice. "Y/n, Y/n,  _ _Y/n__." He spoke low and she had paranoia build in her chest. "Do you want to know something?"

She nodded slowly, a gulp making her realize how dry her mouth was and how stiff her body had become. She was petrified. "Killed a man today." He sighed dreamily, "Been awhile." His eyes leaned back on her after his words. "What have you been doing?" With his question he got closer. "N-Nothing j-just drawing."

His hand hitting the wall behind her, she flinched. "Baby, you know I don't like it when you  _ _lie__." He fisted her hair, pulling her head backwards. "You think you can go touching anyone you please?!" He yelled in her face and tears sprung loose from her eyes. His other hand coming around to grab her neck in a death grip. Spit was on her face from his sudden out burst and she wished Dean was there.

A man only a little older than her walked in, supposedly one of John's goons and looked at the fearful teen. Although she was ignored by the trench coated man and she felt John become more irritated at his arrival. "What Castiel?" The man, now know as _Castiel_ , cleared his throat. "Your wife's down stairs and demands your presence." 

As the two of them pass the mystery man, she didn't dare say a word. This wasn't the first time this Castiel guy had walked in. She supposed he was a good man by the sympathetic look he gave her. Once out of the office she spoke. "John i'm-" He cut her off with a splitting smack. He huffed and inspected the mark, patting her chin lightly. "Don't worry,  _ _cupcake__. I've got a surprise for you later."

He didn't sound nice, the idea of this surprise made her stomach churn and twist. Once down stairs she greeted the women of the household. "Good evening mother, I hope your day was pleasant." She hardly recognized the young adult before she watched as John descended the stairs in a disheveled state. "Wow honey, you start the fun without me?" He chuckled at her statement, before turning back to the one abused. "I hope you greeted your mother the proper way." Margret smiled, though she hadn't a clue what went one between her spouse and daughter. "Yes sir, I would never purposely disrespect."

He didn't seem satisfied with Y/n's answer but left it alone. "Why did you need me down here hot stuff?" He slapped her ass as he walked towards the kitchen. And the two women followed. "Is Dean not here?" You opened your mouth to speak back at your mother, any excuse would work.  _ _Think, think-__  "Yes ma'am sorry for my late arrival." She waved a dismissive hand at the boy.

"Good why don't you two run along and- uh do something." Her hand made way to John's belt. "Bond or whatever." Y/n wanted to snort at how stupid her timing was. As she listen to her mother John gave a warning glare at the two young adults.

She set off to her room, not forgetting her note pads on the way back. Dean tried to speak to her, but she walked past him. "Hey are you okay?" He almost skipped behind her to keep up. She had noticed the bruises she made, but also the new ones. They didn't seem to be made by mouths, not hers anyways. "You don't regret the other day do you?" She set out a long breath, her hand shaking as she steadied herself on her bed. "No, I'd never. It was the best id-"

She shuddered. "It felt good. I don't regret it." Her eyes met his and they teared, "Never." His eyebrows creased and he walked over to put a hand to her chin. Lifting up he saw the sorrow, the pain and bent down. "What's wrong?" She straightened her back at the sound of a door close a few rooms back. She remembered the surprise she was supposed to see, and gulped- anything to get her out of this situation. "Thank you for reassuring me Dean, but I have somewhere to be." 

He made his way to follow her in hopes to get an answer of why she was acting so weird. "Please don't follow me. I-I need to be alone." With that said he stayed behind as she made her way to John's office once more. Already guessing it wasn't going to be anything good, she looked to John as he sat at his desk. "I'm ready for the surprise now sir." He grinned and spoke to her. Y/n pondered that maybe mother forgot something where she had been last. "Well let's get going, cupcake."

The moon was out by the time her and John made it to a lake. The body guard John requested come with them getting out first to open the door, the driver- Castiel, stayed behind. "Thank you Eric." John spoke and looked at Y/n expectantly. "Th-Thank you." The body guard nodded and stood off to the side. "You see that river, baby?" She nodded, and he leaned to her ear. "I want you to drown that man." He pulled from her. "But-" A rise of his eyebrow made her pause, he was eyeing her body. "Take your clothes off." 

She stood there for moment. What was he asking her? "Did I stutter, doll?" Her eyes shifted to the redhead, he was built. How would she even get him in the water. Nevertheless she tried. Her hand met Eric's and his eyebrow rose. The guard looked to John questioningly, but the elder nodded for him to follow. 

John trailed behind them lightly, not to close not to far. Y/n pulled her shirt over her head, reeling in the man's attention even more so. After the clothes were discarded they both fell into the water. "Dunk your head." He listened to her, he was obedient. At his moment of weakness she took a large rock from the shallow water and hit his skull. Once, three times, five. And now he was sitting his head leaking the crimson color against a shallow part of the river.

"Sh-hh shh." She spoke broken and John chuckled. "Just sit." The disabled Eric didn't do as she said and she grunted, having trouble getting the job done. John started to walk closer, impatiently so, pulling a knife from his pocket and a huff left his lips. The body guard realizing what was happening, started to squirm and scream.

John took him by his hair dragging his head from the water and looked to the shivering teen. "Take the knife. Slit his throat." His tone was dark as he held the blade out. "Take the fucking knife!" Y/n rushed to do as she was told. She placed the blade to his neck. Pushed hard and yanked her hand, she flinched as her face was sprinkled with warm liquid.

"Good girl." He praised, forcefully placing his lips on hers and she played into it emotionlessly, no longer caring. She prayed and prayed that night that she wouldn't end up like  _ _him.__ Though God didn't really have a record of siding with her. She'd never kill again, she made that promise. "Castiel, clean this mess up." The man who drove listened to the boss. And the two were back in the car once again. Hands on curves and watery eyes.

_PRESENT_

"I could've done that Y/n." She stood in front of the fire with a stone face. The smell of flesh burned and her nostrils flared in disgust. Her jaw set at the man's words. "I'm not helpless anymore,  _ _Angel__." She threw the gas can on the fire, not worried about being burnt for she was a good ten feet away. "Castiel, clean this mess up-" She stalked back over to the car, "When your done, I'd like to pay a visit to your brother."

**Notes for the Chapter:**

> This is one my favorite chapters to work on and gosh i hope you do too :)))


	6. Chapter 6

_She looked towards the clock as she woke. Oct. 15 '05 12:13. "Lucifer. You have an auction at three today." She spoke sweetly into his ear when she turned around. "Mm- An what time is it sweetheart?" She loved that nickname. "Twelve, we better get up." She sat up, though the calloused hand wrapped around her waist and she giggled as she was pulled down again. Pecks and kisses were scattered across her face, laughs continuously pouring from her lips. He sighed, "Okay now we can get up."_

_Her face held a puzzled look. "Why are you so good to me?" The question was genuine and he paused as his chest tensed. "Well, I believe-" Lucifer rose a hand. "Religiously, that if someone was anything but good to you they deserved to die. You know that." A nonchalant shrug left his shoulders, she couldn't help but smile. "Thank you, Luci." It was the first time she used the nickname. "Never thank me for the truth, cherry."_

_After the auction Lucifer walked into the bedroom an angry expression on his features. "What's wrong?" Y/n exclaimed slowly. "Nothing in this universe is worth my time or talent!" He looked at her and yanked his tie from his neck. "Nothing!" She tried not to take it as a personal jab, "How much?" He said nothing for a minute, a hand running down his face. "Fifty." She stayed sitting as she continued with the new information. "Million?" A shake of Lucifer's head gave her a sinking feeling. "Thousand."_

The seat she sat in was adorned with red velvet. A woman beside her talking the blondes ear off about something a lot less important then why Y/n was there. She cleared her throat and the bimbo straighten with offence, the man she was talking to was humored by the interaction. Y/n didn’t worry for she didn’t have bad ends with this man, but for Castiel the situation was scarcely the same. It didn’t take a lot to worry the trench coated male- and for expressions, usually the guy was stoic. 

Only on few occasions did Y/n ever see him in a light as that. “Well, well, well.” The blonde spoke, leaning forward in his chair and finally disregarding the skanky young lady. “If it isn’t a goddess- and a brother.” Y/n almost smiled at the grin on his face. Despite the name the man had been given he was harmless, to an extent. “How’s the Winchesters, I hear there’s a dispute?” His head tilted, and he had a snarky smirk on his features.

“Lets get to business, I'm not here to gossip.” He pouted. “I don’t think you know what’s happening then? It's quite important.” She could barely get her mouth open to question before he spoke. “What are you here for darling and why’d you bring the grade–A suck up?” With that, a glare was shared between the brothers, and the woman between them pushed on Castiel to sit back. “Just want to know the bidding over John Winchesters land.” He was cracking his knuckles and she sat lost by the sound, memories invading her mind.

__“Don’t worry, that’ll be the last time you see him.” His fingers cracked, and he stared passed her as she listened. She clenched her jaw in worry but all she could do to stop him from getting up, was sit across his lap. “Y-You can’t kill John Winchester, trust me.” She spoke._ _

__"__ And why do you need this information? Do you think that's why they're bickering?” Lucifer had a glint in his eyes as he asked, rubbing his hands together like he had just won the lottery.

“Maybe.” She said hesitantly. It took him a moment to withdraw the information, the glint in his eyes told her that he was hiding something. Though he wouldn't say what in front of Castiel. “Five hundred.” She sat back. “Million?” His chuckle wasn't rude or mocking, but he hated the memory of her and her words, he missed her.  "Try billion." She nodded getting out of the seat and signaling Castiel to do the same. “What will you use the information for?” God, he wished she’d stay.

“I’m not fully sure yet, Lucifer. But the information alone is- is another piece to the puzzle.” She paused and turned back to the blonde male. “And just a favor from you Luce?” His chest tightened, eyes shining brighter than before. “Would you have Dean over discussing this matter? I’d like it if you hadn’t told him I was here, personal reasons.” A kiss to the cheek and a nod of the head, the two partners were headed away from the crooked auctioneer. “This wont be our last errand of the day Castiel.” Her facial expressions were hard and angry as she signalled the driver.


	7. Chapter 7

Castiel kept looking between her and the road ahead of them. "Miss, I suggest we prepare and equipt ourselves with armor before we storm into Mr. Winchester's territory." He seemed worried. No there wasn't any time, they needed to be quick. The meeting wouldn't last that long when Dean figures out it wasn't important. She was desperate, she needed to know why. They were so close. Could this be her fault? She yelled back a reply. "I don't-" A grunt from his lips made her pause and collect herself. "-need your advise, Castiel."

The car pulled up a couple yards away from the building, guards littered the rooms. Every once and awhile a head would check out of a window. There was a couple of men in the front securing the gate, _Damn it_. She sighed as she got out, Castiel right behind her.

"The guards in-" He cut her off. "Got it." With that the two of them made way to the door. "Sorry Tut's, but the boss it out right now." She fixed her gloves and smiled. "I know." A nod left her as Castiel did as said. "When your finished I'll be in his office." She creeped down the strip club hallway once again, before finally reaching the door.

"Unlocked?" She scoffed, "What a dumb ass." When she made it into the 'office' she pushed the end of the oak table. When the desk was moved fully she heard feet underneath the carpet, maybe some soft weeping. Her jaw clenched and she tore at the noticeable seem, finding a little pull handle. There was little light but she could make out a figure.

When she stepped down the cluster of stairs Y/n reached around for a light switch or chain. Eventually she found the latter and saw a familiar face. "Eileen?" Y/n sounded hurt, she really liked her. "You have to be the reason of this _petty_ war." She spoke more so to herself, for the girls mouth seemed to be sewn shut. "Well, how do we get you out of here?" Eileen felt around the hips of Y/n, tears falling from her emotional eyes.  Before Y/n could ask any questions, Eileen quickly found the gun from her waist band and pointed it to the bottom of her chin.

"Wai-." With a shrug and a silencer the woman fell to the floor, limp limbs twisting together as they laid to rest. Y/n shook looking wide-eyed at the lifeless body, she was a good person- an _innocent_ person. She leaned down to grab the gun from the poor woman's hands and scurried back out from under the floor. Castiel gazed at the splattered blood on the wall and turned to his sad and shocked partner. "Shall I clean it up?"

She was pulling her hair back, trying to contain the emotion that pleaded to bubble outward when she replied. "No, I want him to see."

"I'm glad your out of the life Sam." She spoke on the phone with him, Lucifer was do back any moment but she was sure he wouldn't mind. "Yeah, thanks by the way. I would've never made it out if you hadn't pushed me too. Even if he had a plan." She smiled a little feeling more guilty than relieved.

_"So," She carried the o for a while. "How's the one?" He chuckled at her emphasis. "She's doing great, teaching me more and more each day." He sighed and she felt as though he was holding something back. "What's on your mind, it's like I can feel your sad boy vibes." She giggled a little, and he smiled on the other line. "I miss you- our times together."_

_Sam and her had an innocent love while living on the elder Winchester estate. "Me too, Sam. But Eileen is good for you, and I'm still hanging around The Bad and The Dirty." There was shuffling on the line. "So does that make me The Good?" He asked and Y/n tapped her thigh chuckling quietly. "No- I'd say that's all Eileen." She smiled as Lucifer walked in the door. "Maybe I can meet her when it's all over, send some videos. Love ya Sammy, I gotta go." She hung up before he could say it back and he closed his eyes with a sigh._

"Another potential reason."  She told Castiel walking slowly and he nodded obediently, "Possibly." Dean was sure to find her body and know it was Y/n's doing, but she had no idea how he would counterattack. "Get ready for a ride of our life." She thought back to the first time she met Eileen.

_"Yeah I've been through some tough things." Y/n patted her belt buckle, so it seemed, and Eileen gave a confused yet understanding expression. Sam had left for the moment and Eileen had asked of her past with the man. Maybe Y/n gave a little too much information but the woman in front of her was way too easy to talk to_.

_"I've got a gun in my waist band-" Y/n chuckled a little awkwardly lifting her shirt to show the girl. "Ohh, that's good- I guess." Eileen smiled as she spoke, Y/n reciprocating the expression. "Well it just for protection so don't worry."_

"Leave the desk where it is." She said walking leaving the small room and walking past the couple dead guards who let their loyalty get in the way of their life. She shook her head at the building once she got out, letting her expressions form unforgivingly hard features. "Shame."

**Notes for the Chapter:**

> Please let me know if the story or plot so far is confusing, so I can fix any mistakes !!


	8. Chapter 8

That night she waited by the phone, though when the sound she wanted came, she hadn’t the heart to pick it up. The leather that she sat on stuck to her thighs, the phone by her yelling impatiently. Castiel groaned, “Will you  _please_  answer. You know he isn’t going to stop calling.” This was true, Y/n looked towards the flashing screen.  _Dean,_ of course it was Dean. She answered the phone with creased eyebrows. “You killed her?” It was a faint question, she could barely hear the rise in his voice. “No, she  _shot herself_.”

Y/n spoke plainly, hiding her own pain for the women that shouldn’t have been dragged into this. “Your sick, you know that.” She said to him and the line was quiet, other than a woman’s giggle in the background. “Sweetheart, everybody’s sick in this business.” She shifted herself at the nickname, it reminding her of old times.

“Is this little-” She paused to put a sneer on her face. “ _Spat_  about Eileen?” He sighed. “Nope.” Her jaw ticked, “Is it about me? Is this about us?” Dean didn’t say anything for a while, the woman’s giggles finally gone. She felt stupid for even asking but she  _needed_  an answer.

_“You really told Sammy to leave me?” He sounded so broken, the tears in his eyes reflecting her own. After a moment of her not saying anything to the rhetorical question, he spoke again with finality. “We clearly know who your favorite is here then, huh!” When she still refused to reply his hand whipped at the lamp on the bedside table._

“No,” He had a shaky breath come after it, “No sweetheart it isn’t.” He chuckled a little and she could feel his heartbreak through the phone. “It’s about the Winchester property then isn’t it?” He laughed loudly this time. “Are you really asking me this?” He paused for a minute, seriousness lacing his words. “After everything that happened? When I found out I-

"No. At least not for me, never. I can’t say the same for Sam. You should check on that.” She sat there a little confused, racking her brain for another reason.

“Then  _why_?” He huffed and there was shuffling on the line. “Why are you trying to stop us- me. Y/n, this- this  _needs_  to happen.” A hand flew to her forehead and massaged her temples. “Dean-” He cut her off with and obnoxious sip, of possibly whiskey or burben. He was getting angry that she wouldn’t just drop it.

“Your a little naive to get that your not wanted.  _Clearly._ So stay out of it. Simple. If you truly think we’re having a spat about  _you,_ then _you_ choose _._  Stop trying to have us both, it never worked before.” She shook with emotion, not really feeling just one in particular.

Though her distaste was so powerful he could feel it through the line. “Your a lot like you father, Dean Winchester.” She heard a displeased grunt. “This is one of the most-” He cut her off again, this time with a gravely voice. “Then, since your so adamant. Let’s say it  _is_  about you.” He chuckled darkly.

She leaned back, the chair squeaking impossibly loud. “What would you even do about it?” It was a question meant to hurt her, burn her efforts and she could see that. Silence followed his words, “Exactly, don’t worry your pretty little head and let the big boys figure it out.” A sob wracked from her chest. He made her feel so hopeless. “This is dumb-”

She took in a shaky breath calming the knot in her throat and pleas within her words. A wavering voice that told Dean she needed him by her. “You’re  _brothers_.” It was a choked out whisper, and he flinched away from the phone. If she could see Dean’s face she would know that he felt the same- that he thought this was stupid too, to some extent, and that it was all his fault that it had escalated to this. But it had to go on. “Not anymore.”

The line went still, her heart going faster than a race horse. She stood looking frantic. Castiel moved to stand with her but her glare kept him grounded. “Don’t. Follow.” She sighed reaching the door. “You’ll make things worse.” The last thing she had in hand was her gun.


	9. Chapter 9

NOVEMBER 20TH 2006

"I haven't spoke with Dean since I left." She sighed at his confession, laying on his chest she could feel his raised heartbeat. "He'll forgive you." She spoke so surely, so he thought, that he smiled. "I'm happy that I took your advice and ran. Though it's been hard without him, he was my _life line_. My _anchor_."

He paused running his hand threw her hair seeing her naked body under the thin sheet. Changing the subject quickly, "And I'm not happy your with someone else and not me." He spoke and you chuckled, "Since when was Sam Winchester a relationship status guy- and anyways if your going for that you have Eileen now."

He didn't seem happy at the mention. "I like her I do but-" She nodded dismissing the subject and patting his chest. She turned over and let the tall man spoon her, a sigh leaving his lips and traveling across the back of her neck. "Have you at least talked to him recently?" She knew he wasn't done and she didn't dare speak word of her deepest conviction. "If your here and I'm here, then he's all alone- he's probably being bombarded with blame."

She sat up suddenly and gave a hard stare at the sheets. "No, I haven't spoke with Dean. Fuck, Sammy no I haven't okay-" His eyebrows creased, waiting for her to continue. Watching her run fingers threw her hair anxiously. "That's heartless I know, but-" She clutched the thin fabric closer to her chest, tears over flowing her eyes. "I let you go and- and he was so hurt. He spent so many nights with me and I let him. Fuck I felt guilty so I laid with him. I got hurt so many times because of my doing, Sam. Its all my fault. You can hate me all you want but please-"

She paused to look at him, the tears in his eyes straining to stay in place. And although he didn't know the whole of the situation, he felt for her. "But please, don't let me be the reason the two of you can't come together again. I can find him- bring him here." She now was looking to the curtain hopefully.

"You can reunite and I can just go missing, I've done enough already, I should've left it alone. He had a _plan_ , why'd I _fuck_ with our plan?!" He couldn't admit out loud that the last bit perked his curiosity up a little, but nevertheless he placed a hand on her shoulder to keep her from rambling. And rather than asking the question on his mind he went to console her.

Just as he was about to speak a harsh knock landed on the motel door. He groaned, kissing her temple. "Breath. I'll be back, that's probably just the food." He jumped up and tossed on a pair of loose boxers hopping to the front door. When the hinges squeaked and the man on the other side was revealed, an angry glare and a fist was thrown at Sam.

She had no words as the taller of the brothers hunched over in pain. "Don't worry, Sammy, I got the food. Pay the girl, we-" Dean pushed past him as he spoke. He looked only slightly surprised to see her in his younger brothers bed. " _Wow_." He paused, swallowing the lump in his throat.

"I mean, I hoped you were better off-" He tossed the brown bags to the floor, watching her look anywhere but his eyes. "But I didn't know you- you left me for Sammy _?_ " He growled as she stole the rest of the covers to hide herself. "Look at me!" A shudder left her, tears falling slowly but steadily. She listened to him and looked into his emotionally damaged eyes.

"Dean-" A hand shut the younger brother up. "You left me! With an abusive _criminal_ , who wholeheartedly believed _I_ knew where _you_ were! _And_ Sammy. Oh, but the beatings were always the worst when talking about you."

His breath was ragged, fists clenched at his sides. " _Do you know what happened to me_? Even after he died, I was still pretty fucked up!" Sam made a surprised sound and she looked away for a moment. "Hes dead?" There was a silent moment to let the news sink in, but the rage and sadness still stung the air.

Dean let his shoulders slump "I'm sorry okay." He laughed sarcastically. "You're _sorry_? Y-" She cut him off with a booming yell. "You don't know the full story, Dean!" Dean brought his hand through his hair, turning around and pacing. "Look Dean she didn't know it was gonna make you so upset when she told me to leave." Dean's body froze to the spot at the sentence.

"What?" She was breathing harder now her eyes never leaving the enraged frame. He turned back to her, but she silently sat there with fear coursing her. "Y- You mean you didn't-" Sam didn't finish his sentence before he turned to see her. "You really told Sammy to leave me?" He sounded so broken, the tears in his eyes reflecting her own.

After a moment of her not saying anything to the rhetorical question, he spoke again with finality. "We clearly know who your favorite is here then, huh!" When she still refused to reply his hand whipped at the lamp on the bedside table. It was so close to her she flinched violently.

"It- It's not like that." She spoke so quietly they almost hadn't heard her. "Then please enlighten me _, Y/n/n."_ She huffed standing and throwing her clothes back on to leave. Before she made it out the door she stopped by Dean, not looking towards him in anyway. " _Everyone_ was in the same boat. You were gonna be next, then things changed and I'm _sorry_." The boys watched her leave, a new tension rising in the room.


	10. Chapter 10

Surprisingly she knocked and waited as hush whispers were exchanged, a few giggles filling the silence as she waited. She knocked harsher this time and a groan followed. When the door opened Sam wasn't at all the least bit startled when she flashed her gun, but the woman that peaked over his shoulder gasped.

"What a pleasure, Y/n/n." He spoke, no emotion filling his words. Without speaking Y/n pushed past him and the woman on his arm. His stoic facade fell and his eyebrows creased in confusion and slight conern, as Y/n held aim to the blondes forehead. " _ _Leave__."

The woman scoffed and looked to Samuel expectantly. "Nothing personal babe." Y/n spoke jolting the weapon upward, making the girl scurry away. As he sat down he sighed. "What do you come with today?" He was straighting things around his desk, buttoning up his shirt and running hands through his hair.

"Are you bidding money on John's land?" He stopped moving stunned with a questionable stare. "Did you even know it was up for auction?" She sat as she spoke, her business image falling and her more vulnerable side pushing to the surface. "No, is __satan__ selling it?" He rolled his eyes at the name and she chuckled. Something that made him smile.

"What did you bring __her__ for?" Referring to the gun, Sam pointed to Y/n's hand held weapon. "Incase you decided to be a __brat__." He laughed aloud and leaned back in his chair.

"No, I have no clue about what is happening with John's land." She nodded standing and turning to leave. "You know, instead of figuring out what's happening, you could just stay?" It sounded a bit like a goodbye or a desperate plea, a one hitter to keep her just a little bit longer if not more. And when she looked longingly at him, he wished for the latter so badly.

"Instead of hiding things from me you could tell me what's going on?" She said lightly, a calm emotion spreading throughout Sam's office. And although her shoulders slumped in defeat he still held pride over his love for her. She gazed at the room, scanning over everything and nothing at all.

She'd do anything to be in his arms. Dean's too, watching dumb shows and eating junk food. Like the old days. "I'm sorry." She spoke and left, walking out side and to her car. Those times were over, at least until she figured out what was happening. And she had an idea of where to look. Y/n thought about this while on the road, would it ever be the same? Could she have both brothers without casualty?

As she made it back to Castiel, she found him pacing. Worry clouded his posture and doubt wrote his features. "Castiel-" He turned quickly to find a small sorrowful smile gracing her features. He wanted to embrace her loosing frame, but that would be inappropriate. At first he thought the chuckle she let out was genuine and it was almost enough to reassure him.

That maybe everything was fine, maybe everything would __stay__ fine, but the words next make his chest tighten and his head cloud over with anxiety. "I need to speak with Charlie." If the quick witted redhead was getting involved, it would mean things were only just starting.


	11. Chapter 11

The apartment hallway made her stand out, she looked as if she was planning to go to a ball. Castiel on the other hand liked her outfit, it fit her curves, was she dressing up for the hacker?

Y/n knocked lightly on the wooden door, although loud enough for the redhead to hear and when the door opened a loud greating came from her mouth. "Charlie Bradbury! The woman I love to see in action." She leaned in to hug the redhead, her personal guard dog hovering over her.

"Y/n Y/l/n. A woman I love to do business with." The hacker spoke, throwing a wink and a nudge Y/n's way. Castiel cleared his throat interrupting the moment. Charlie groaned, waiting for the trench coated man's input.

"We've come for _information_." Charlie scoffed at his annoyed tone, "No tea then, _Cassie_?" She spoke sarcasticly before setting up her station, and getting to business. She looked up to Y/n a crease in her brows. "You mentioned briefly on the phone that it's about a property of sort?" Charlie questioned and she nodded. "Yes John Winchester's, property there should be about a five billion dollar offer."

The redhead scoffed as Y/n spoke, "That price seems made up, it's very _very_ high." Her eyes were trained on the screen in front of her. "So the auctioneer who is selling it is unknown to you?" Y/n shook her head, hands nervously picking at the hem of her clothes. "No, it should be auctioned off by Lucifer."

Charlie typed at her computer for a good five to ten minutes, before she pumped her fists in the air- a celebratory 'hell yeah!' echoing in her house. "Looks here that neither of your boys were lying. The property is being bought by a man named Crowley."

She paused eyes flicking across the screen. "He's vaguely in contact with Lucifer, in fact he seems to be making all the negotiations through another man who's name is unknown."

Y/n could sense the tension leaving her angles body. "Is that all that's spoken between them? The auction or the property?" Charlie shook her head, eyes widening. "Looks here, you have much more to worry about than a petty rivalry."

She paused, her obnoxiously noisy mouse irritating her guests the more she scrolled. "I mean I'm talking multiple deaths, plans on how to keep them dead. The list goes on. It's says here Crowley spoke of you on many occasions." She tapped her fingers on the keyboard and search for another moment.

"I'm also seeing that he's known to communicate between the Winchesters. Not only your boys but Mary as well." _Mary Winchester,_ she thought _wasn't she in jail?_ as Castiel jumped from his seat, pulling Y/n from hers suspiciously. "Let's go." She nodded her head, eyebrows furrowed.

She said a short goodbye to Charlie who only waved, as she was glued to the new information she had acquired. Y/n on the other hand had her eyes glued to the man  that walked in front of her, he was looking around them franticly moving.

"Castiel?" She asked as they walked their way to the car, she was ignored and he held the door open for her. Trying and failing at prompting her to move a little quicker. "Do you remember what you told me when you found me- after John, after Lucifer?" She could practically hear his nervously gulping as she stood beside  the car in a patient manner. "I do."

_"Y/n, I vow to protect you with my life. I should've- this should've be done sooner. John was-"  She shushed him, only silencing him for a moment. "I won't leave you alone again, I'll help you. If you will trust me?"_

He almost shuddered at the intimate moment. "I would never back out of an agreement, a promise." He said as they sat against the leather, "I am yours, Y/n." He could see the vulnerable woman he vowed his life too in that moment. She was smiles and tears at the corner of her eyes. But nevertheless he nodded. " _Good_." And she smiled, sending only a little bit of relief his way.


	12. Chapter 12

Even with the reassurance and the words they shared beforehand, Y/n still felt as though something was being hidden from her. She would look to Castiel every other minute, trying to decide on what was going to be said next.

The trench coat he wore was wrinkled, that was different from normal. She studied him for a moment, his built arms constricted by the fabric but not buldging out. She could tell that his breathing had picked up, his eyes catching hers as they looked out of the corner. Each time they did she grinned a tiny bit. She must have had adoration in her eyes, he looked a bit flustered.

She chuckled and crossed her legs, she had to charish the good moments. They were hard to come by.

Eventually it was the blue eyed man that spoke. "You have something on your mind." She nodded, of course she did. _Many_ things. When didn't she. "Why did you pull me out of there when Crowley was mentioned?" Castiel looked at her confused for a minute before a knowing look made way to his features.

"We shouldn't get involved with him." She hummed, irritated. "What if _he's_ the reason they're fighting." She waited for a response from Castiel for a brief second.

"That would be the only way _I_ see this worth it." With a finger to her chin she contemplated the reasonings. "Maybe they know about him buying the land-" Castiel said her name softly trying to get her attention. "But that wouldn't make sense, they've both shown no care for that _hell_." He spoke to her again a little louder but her mind over powered the man's voice.

Her face was pulled into disgust, with her small reminder of the home she once lived in, as she tried to continued. "I just can-" He raised his voice even _louder_ , effectively catching her attention but she flinched _hard_ on herself. "Y/n!" The crease in her eyebrows was one with more anger than worry. "What?!" She roared it out.

"Their _spat_ -" He paused looking over her with piercing eyes. "Is not about Crowley, and that's _not_ what we should be worried about!" They only shared challenging gazes moments afterwards. The driver was anxiously taping the steering wheel, looking between them and the rode.

"Then what?!" She waved her hands around, hair falling into her face and her neck red from frustration. "Since you know all, why?!" When he refused to answer, looking away from her, she questioned once more. " _Hmm_?!"

Her eyes were wild as she sat in suspense, his back turned too her and finally she had enough. She pushed his shoulder into the car door, white hot adrenaline fuelling her. "What do you know?!" It was broken and raw, her voice rough and it hurt Castiel more that the low throb in his shoulder. "Mary Winchester!" He answered hoarsely.

She moved to push him against the window again, but he caught her wrists skillfully. "Mary Winchester." A couple of breaths later and all rage disapated from her body, replaced by sheer curiousness. "Isn't she in jail?"

He nodded, releasing her with only a tinge if annoyance. The driver was confused at how quickly they had forgiven and forgot their argument. Even slightly grinning at each other. "Why would they feud about _her_?" She questioned herself more so than the raven haired man. "I understand that she's their mother, but-" A small hum escaped her as they pulled into their driveway.

"Do you-" Before she could question her reliable source, he answered. "Shes leaving jail three months from now." Understanding took over her whole body, though only for a moment.

"I though she-" Again the blue eyed man finished her sentence. "Sentenced for life? She was." He paused moving out of the car, she waited for him to open her door and when he did he spoke once more. "She just has strong connections."

An 'ah' left her mouth. " _Crowley?_ " With a nod, he lead her to the front door. "Why would Mary, of all people, bring a war between her kin?" Castiel looked away from her quickly, a gulp running down his throat as he replied with a lie. "I couldn't possibly know, Y/n."


	13. Chapter 13

Dean missed her, _bad_. Every time he saw her name he'd hover over the button with his thumb. He wanted to talk with her, ask to turn back the clock. _Anything_. The women he brought back, never had anything on Y/n.

The phone was once again in his hand this night, he looked at the photo the two of them set up all those years ago.

_"Dean, stay still!" She giggled as he shoved his face into her neck. "Come on baby, it'll be cute for the picture." She huffed and erupted into laughter once again. "You better stop making me laugh or were gonna wake up John!"_

The rest of that memory was horrid, and he shook his head bringing his features back to a small smile. He clicked on the photo, he never had the heart to erase it. So what if she was with Sam, could they not share?

Even if they wanted too, with the current events, they were out of luck. He sighed, sinking farther in his seat and gazing longingly at the picture. He missed the somewhat carefree Y/n. She always knew what to say, always knew how to make him feel better. How to make him squirm and moan. He groaned at the thought, going to their texts.

'Hey' It was simple and it was most likely going to be ignored. But nevertheless she replied. ' _Hi_ ' He could practically see her facial expressions, eyebrows creased with care and loneliness. 'Can we-' He changed his mind suddenly and deleted the few letters he had.

He thought for a moment, tapping the side of the phone. 'Do you think we will ever be able to start over?' He meant the near future, he didn't know whether or not he'd be here for too much longer. Although he hoped so.

Maybe being forced out of the life wouldn't be so bad. Maybe they could have a life together, he knows she's always wanted something like that. But he knew the terms and conditions when he and his mother talked. There could only be one Winchester boy as head mafia.

'Well, that depends.' She texted back quickly and he let a chuckle slip past his lips, not ready for what was to come next. 'Is Mary the cause of all this?' His heart dropped at the words he read. She figured it out. Of course she did, she _always_ did. 'Yes.' He sent not seeing or feeling the need to lie.

'Why?' He was a little confused by her questions, more so at the call that came quickly after. "Hello?" He spoke hesitantly. "Dean-" His breath of relief at just hearing her voice sent waves down her body.

"Why does Mary getting out of jail cause something like this?" She didn't let Dean answer. "Im only so- I feel like something _bad_ is going to happen, don't let your mother kill your brother, or you." He let her finish before he comforted her.

"Sweetheart, neither of us will die." He said, but uncertainty lined his words. "Dean. Tell me why Mary plays a part in this." It was a demand and his fingers tingled at the tone in her voice. "Once she knew she was leaving the joint, she contacted me. Then she contacted Sam."

He almost gritted the last sentence out, not liking that his mother felt the need to contact the younger Winchester as well. "She stated the following, _clearly_ 'Either one of you _take_ the others title, or I choose one and kill the other.'" He let the information sink in before he continued.

Hearing the small gasps made his heart lurch forward. She still cared. He knew that from the beginning. "What's- what's that mean Dean?"  He ran his hand down his face wiping tears he didn't know he let loose. "Princess that means its either me or Sammy, one of us has too go." She sounded nerved with the sound that cam from her throat.

Millions of questions ran through her mind. Do they only have to give away their title? Wouldn't that be easier than loosing their life's? "So one of you let the other have the stupid podium and come be with _me_?" He smiled, he loved the sound of that.

White picket fence, green yard that always seemed to look better than the neighbors. A couple of kids, he'll maybe even a dog. Soon his smile faded. He couldn't do that, every one knew Dean had a soft spot for Sam and vice versa. They would use Dean for leverage any chance they'd get. That would be putting Y/n in danger and whoever else they decided to bring with them.

"It doesn't work that way."

When the phone was hung up Castiel set a cup of what seemed to be alcohol next to her. "We don't have any plans tomorrow, drink up. Let loose." With his words he tucked some hair behind her ear. "As long as you fall down the rabbit hole with me." She suggested, a small smile in her lips as she held the cup up.


	14. Chapter 14

**Notes for the Chapter:**

> :) cas smut : ) ( : : ) ( : : )

The drinks that slid down her throat made the man chuckle and laugh beside her. She was drinking like a maniac as he made sure she didn't do anything crazy. "Maybe you should take a break." Castiel spoke hesitantly but she only leaned into his side and his voice.

She slurred incoherent words, he struggled to listen. She was almost in his lap, and as that was a distraction in itself, the words that flew from her lips made his body tense. "Maybe you-you should kiss me." He didn't want to say no, but his morals weighed his decision.

"Your drunk Y/n." She shook her head and leaned in, she barely had a moment of his lips on her before he moved her to his lap, standing. She played with the strands of hair at the back of his head and ran her lips down his throat. He grunted finding where he was going.

Castiel dropped Y/n on the couch and walked back to where they were previously, a glass of water in hand when he returned. "Your too- Your too good to me." She hiccuped the last part. Taking large gulps of the water, she pouted.

Although she was wasted, she could feel the others vibe coursing through her. He was conflicted. "You know-" She started. "I have always seen your eyes when you looked- are looking at them- me." She struggled to get the right words off her tongue and she moaned in discontent.

"Just for tonight, let me be good too _you_." With the big eyes looking up at him, his stomach flipped and the water was taken out of her hands. "Y/n, if we do this. When you wake up, _please_ don't pretend it didn't happen." Castiel had had a few drinks himself. Not enough for his inhibitions to faulter, but enough to taste the liquor on her lips and groan.

He pushed her shoulders back to where she laid. "Now-" He tried to get out but her nails drug down his chest and he stuttered. "I- ugh fuck it." Her hands were pinned forcefully above her head, his lips leaving bruises all along her skin.

The action had sobered her up just in the slightest but his movements seemed to intoxicate her in different ways. "Cas-" She moaned as his hand slipped up her dress. When Castiel reached the silk of her panties he rutted against her thigh. "Fuck- did you get all dressed up for me?" His nose was against her pulse point, his lips dragging along her smooth skin as he spoke.

"Yes-" He let his finger trace the inner folds of her core and her back arched in anticipation. "Yes _what_?" His husky voice did wonders to her body, her nipples hard and she clutched at the couch as much as she could. "Yes _sir_." He shuddered at the sultry voice she gave him. She could be the death of him.

In a swift movement her silk dress was pulled from her body, the cold air hitting her breast as the cool eyes looked her at her intently. Now seeing the younger woman fully Castiel felt a little guilty. Nevertheless he ran his hand down her stomach and watched as goosebumps followed. "Please Sir, m-more." Blatantly ignoring her Castiel leaned down to pull at her underwear with his teeth tauntingly.

She tried not to buck her hips, but when his nose skimmed the wet lips of _her_ , she whined out, moving her hips upwards sharply. "So _sensitive_." He moved his hands to her inner thighs and spread them apart.

A broad lick of his tongue against her cunt, tore a ripple of a moan from his throat. "You taste _so good_." Pleading his name, she tangled her fingers in his hair and pulled his face back towards her. Finally he relented his teasing and dove for her clit, finger moving feverently, his actions made her legs shake and twitch.

With heaving pants she let out a stiffled purr. "Uh- Cas i-" He sucked at a place between her jaw and eat, when his name reached his ears. He was finally getting to show her what she deserved. That thought by itself almost made him finish. One of his hands reached down to grab his shaft through his pants, the growl pulsing through his body and on to hers.

With the sound of pleasure he gave she clenched onto nothing and let a husky moan coat the ears of anyone who listened, signalling her release. Castiel pulled his member out of the top of his belt, he was angry red at the tip and Y/n whined at the sight. He was way bigger than she could've hoped.

Almost involuntarily, she spread her legs as wide as they could go. "I want you raw." She whispered out, a short nod coming from the man above her and in one long stroke he was bottomed out. A synced sound came from the two. His pace picked up quickly. He was focused on her pleasure, but he was _so_ wrapped up in his. There was no rhythm; No continuous pace, but her back arched when he hit her best bundle of nerves.

Her legs wrapped around her angles waist and she moved his hand to her throat. " _Please_." She wanted out one hand on his chest and the other massaging her breast. A vulnerable whimper excreted from Castiel mouth at her plea and he gripped around her neck roughly. As she came his moans got louder, her walls clenching his cock and making him cry out in a begging manner.

With how sensitive she was and his pelvic thrusting against her clit, she was on the edge of another orgasm. "Don't cum yet." It was exclaimed sternly and she nodded at the order. She twiched around him and with a final thrust he growled aloud. "Now." Y/n threw her head back as her pleasure kept going and going, her body guard filling her aching core.  

"Cas- I'm so-im se-" She moaned again. He pulled out after and took satisfaction in seeing the mess she had made. He swiped two fingers through her folds before placing them in his mouth. He lent down to capture her mouth, biting her lip ever so softly.

Their foreheads leaned on each other, "Thank you." He spoke, and she nodded a hand cupping his cheek. Even if the couch they had messed up was small, he squeezed his body in beside her. Her eyes were half open and chest tucked close to his, "Your very precious to me." He whispered out and she hummed back, asleep. Would she remember this in the morning?


	15. Chapter 15

Dean decided to make a surprise visit. Knocking on her door was hard, but it had to be done. Whether or not he'd make it out of this whole thing or not, he had to see her, hold her, love her. Just until he couldn't anymore. The first knock went unanswered, she was still tightly wrapped up in Castiel. Another knock sounded throughout the tiny houseand Castiel groaned in the crook of her neck his teeth scraping against the skin before he got up to answer.

She moaned at the loss of his warmth and he smiled. Maybe he'd have her s his? When he made it too the door, boxers the only thing covering his body. He held a hard face when his eyes met green once. Castiel rarely showed emotion when it came to someone other than Y/n but the pure disgust he held for the man in front of his was too hard to hold in. "Where's Y/n." Dean spoke harshly, a sneer strewn along his features.

"I'm awake, let him in Castiel." She had the long couch pillow covering what Castiels shirt couldn't. She'd be lying if her heart rate didn't pick up at the possessive look Dean gave the raven haired man, or the way her heart dropped at the hurt that flashed across his face when his eyes met hers. "Can we-" He trailed off, looking at the living room filled with trash from the previous night. Clothes and bottles of alcohol thrown around. "Talk alone?" She could see the way Castiels shoulder  squared at the question and she pulled a hand out to cool her guardian, no doubt infuriating the mafia boss in front of her.

"Of course." It was the kindest tone she's given in a while, moving the pillow and making room for the man who didn't move from his spot. He was wearing a washout green jacket with denim underneath. Casual for him, but nevertheless looked amazing. When Castiel left the two of them were encased in silence. After a while she spoke, "Are you gonna- are you gonna sit down?" 

He looked tired, like he'd been awake all night and then walked the thirty miles it took to get there. "You and Cas now?" She sighed and put her head in her hand. Little did the two know that the guardian was out of sight but not out of ear shot. "I was drunk and it was good for the moment, I don't intent for it too be long term." Dean scoffed and rolled his eyes. "Never disappoint with how many m-" She cut off his insult. "What did you come too talk to me about?"

He huffed and shuffled where he stood. "I-" He walked over to sit on the couch before he continued, not looking her un the eyes once. It made her uneasy, what was he about to say? "I need you." It came out as a whisper and she could see him shaking. " _Your_ the one who broke it off." She replied a little defensive, watching as hands made their way to his face. He looked too her finally, eyes red yet still never catching her e/c ones. "I know. I want to fix it, no- I _need_ to fix it."

She sighed grabbing his face and making their eyes meet. "What are you going to do? I can tell you've given up." There she goes, back to the problem at hand. Mary Winchester, the bitch was back and taking one of her boys. "I'm coming to get you back. That's my first move, sweetheart. Thought I might gain something before I loose everything."

Her heart shattered and she moved to sit on his lap. Almost immediately his head fell into her chest and a sob escaped him. "I can't see her again. Not after-" She shushed him. "We're gonna figure something out." He leaned back a little and let her wipe the tears from his face. "I need too- I wanna tell you." He drew in a shaky breath, relaxing with the fingers she ran threw his hair. "She was worse than him." Y/n's heart sank, and she wonders if she heard him correctly.

"He was the savior back before the power." Although confused, as she'd never seen John in that light, she continued to listen. "Almost every night, she took us on what she liked to call road trips." He laughed a little. "Sam stayed home, I meant we as in me and my step brother. Adam." She had heard of him before, it was tragic. "I know how you think that story went down, but it's completely bullshit. Made up to make her look good."

He pushed her back a little. "I just need you to hold me, I need to hold _you_ every night. I want you just for a little while, because I know who's gonna loose this and it's not Sam." She looked into his eyes and furrowed her brows. "Dean-" She started. "Let's take a day too think about this." His shoulders slumped. "Just say yes. After it's said and done for you can go and live your life with Sammy or even your little lapdog." She looked down, how was she gonna keep him fighting. "Under one condition." He looked up too her eyes. "You not only keep fighting, but you fight for Sam too."


	16. Chapter 16

Something was going on with Sam. He didn't acknowledge Y/n's texts, ignored her calls. Mary was due out of prison in two months. How she got out of a life sentence was beyond anyone's knowledge. He paced the windowed room, " _Crowley_."

The business man nodded his head in reply, albeit fearfully. " _What do you mean_  Lucifer took the land off auction. You know damn well Mary-" Crowley interrupted his speech with a snarky tone.

"You still call you mother by her first name?" The youngest winchester stood straight, startled a bit by the question. "It's out of respect. Not to mention-" He turned away to grab his chiming telephone from the table behind him.

"She's never really been a mother to me, anyway." He silenced the phone, no emotion in his voice.  _She_  was calling. It hurt him to ignore her, but Mary shouldn't know about his affairs with Y/n. She'd only get hurt.

Or worse.

"Lis-" Crowley tried to speak, being cut off by hands slapping down against his arm rests. Somehow Sam was able to take reign of the business mans office. Demeaning him by sitting on the obnoxiously black oak desk.

All the while having the coward crawl to sit in front of him. Like a principal and a student. "No. You listen to me. Find a way to put John's land back on the market. Or you'll end up like  _your_  whore of a mother." Crowley cringed at the threat.

_"Your father could beat me better than that, boy!" She spit, though her words went unacknowledged as one final blow was delivered to the redheads skull. "Whore." Crowley spit at her twitching frame. Great. Now he had to get rid of his mess._

Goosebumps littered Crowelys skin at the memory. "As you wish Sir. I will try." The younger Winchester grimaced, speaking before walking out of the room all together. "Don't try, Crowley, do." Sam's phone was buzzing constantly, he knew she wouldn't give up. When was Y/n know to leave things be?

He answered sharply, "Make it quick." She was startled by his hurtful tone but the hands that smoothed down her back kept her temper at bay. "I-i wanted to see if we could meet." He pondered for a moment. Of course she'd ask something like that at a time like this.

"Dean would-" She drew in a breath as she waited for any sign that she was being heard by the cold, cold man. "Dean would be there with us. Sam, your mother can't control you anymore your bigger than her."

He scoffed, "You didn't know her." Her brows came to rest together, "Neither did you! And if you had any ounce of time with her then you were a blind four year old Sam! Dean has tol-"

He cut her off as he sat behind the wheel of his car. "Told you what? Whatever you needed to hear so he could get you in bed again?" She grunted on the other side of the phone. "You want to win don't you? You don't care about Dean, ab-"

She sighed. " _You don't care about us_." These words made Sam falter, his heart pumping just a little bit faster. "You were so quick to say yes that day, leave that house. I did it for you, but-- did that change anything, did you only keep in touch because yo-" Once again her rant was cut short.

"Maybe your right." It hurt him to lie, but something had to be done. Even if he had to hold his tongue when he heard the sound of her heart shattering on the other line. "But I don't expect you to understand. This time, I need to finish this. This  _time,_  I  _need_  to win. I can't loose to him again."

She leaned into the hard chest of Dean, feeling his shaky breath on her shoulder. "Dean hasn't won me Sam. I'm both of yours, even if you both don't like it." He hung up shortly after, knowing she'd be in his brothers arms, knowing he'd have his mouth over hers.

He banged his hands on the dash board, a scream escaping his lips. He needed to compose himself. He only had a couple days shy of sixty to win the property over, and he didn't have the best of fellowship with Lucifer.


	17. Chapter 17

Open mouthed kisses landed themselves on her neck, her fragrance _always_ drew him in. "Dean." She moaned, moving to sit across his lap. Distraction. That's what he needed, what she needed was release. "What baby?" A whimper escaped her lips at the pet name.

"Need you. Need you now." His heart jumped out of his chest, bucking his hips, he replied. "Take off your shirt." She did as told and then moved to repeat the action upon him, deja vu hanging flat in the air. "Dean-" He shushed her, attacking her mouth with rough kisses and needy growls.

He leaned back admiring his work on her neck, she was _his_. In this moment, in this life he was leading. She was his. He was so sure. "Wanna suck you off." The plea was breathy and shuddering in his ear. A chill ran down his spine at her confession, a groan passing his lips as she slid down his body. She couldn't get Sam off her mind, she was so worried, but her body was reacting _so_ well to Dean. She needed this.

His hands tugged harshly at her hair, making her bare her neck to him. He dipped down, sucking another mark into her neck like he _knew_ she was thinking of his brother. "Mine." She purred out, in the humid air they created, and he grinned. This was his heaven.

Castiel cleared his throat, the two jumping apart quickly. " _What_?" She snapped harshly. "You have a visitor." The man beside Castiel smiled wickedly. She stood and glared ferociously at her body guard.

"Did you forget what 'do not disturb' meant?" Her nose was level with his Adams apple and he let the corner of his mouth rise the tiniest bit in amusement. Of course she noticed, but before she could say anything Dean spoke.

"I'm assuming you're here for me right? Crowley." The wicked business man nodded, fixing his black satin tie. "Yes, Sir. Your brother seems to forget that I am under the protection of the Winchester blood line. The two of you might not like me, but if he thinks he can even lay a fing-"

Crowley spoke with more amusement than anything, as the elder Winchester cut him off. "And you seem to forget that me and him are brothers." Dean spoke in anger, crossing his legs to cover his stiffened member. Crowley chuckled, "I'm sure even _he_ has forgotten that, boy." 

"Is that all you came here to tell me?" The green eyed man was dominating the room with his presence, the ordering tone in his voice making Y/n's legs quiver.

"No, actually." Making himself comfortable at the opposite end of the couch, Crowley sat and repeated Dean's actions; Crossing his legs over one another. "Mary's release will be sooner than we expected." He said it so nonchalantly that the shock came late.

"W-when?" Dean didn't mean to stutter, and Y/n walked back to sit upon his lap once again. "Next week." Crowley didn't stop his nasty grin, the expression widening with Castiels confused sputtering. Along with everyone else's. "Does Sam know?" Crowley didn't answer her right away. Dean tensing under the curious woman at the knowledge of her concern for his brother.

"No." She hummed, leaning to grab her phone. Crowley snatched the device out of her fingers almost as soon as she touched it, the elder Winchester puffing his chest out defensively at the action.

"Sorry sugar, momma doesn't want little Sammy to know." When she gave him a confused look he continued. "I guess that leaves me to my third and final point." He turned to stare at protective man, leaving Y/n to feel invisible.

"She's not going to let you loose, you know. She's trained you from the beginning, you won. She wanted me to bring the news to you, not to Sam-- and seeing as he sent me a death threat not but a day ago, he wont know until mommy dearest kills him herself."

He stood after that, straightening his expensive trench coat. "Do you really think you'd be out of the life? You can't just disappear and expect it to all just float away. So, good luck and-" He picked up a glass of wine, that had been disregarded hours before, and took a swig holding it to the two of them. " _Congratulations_."

As he was being walked away by Castiel, Dean noticed her hands shaking as she clung to his shirt. "Y/n." He said it softly, but she could tell he was more than a little frightened. Though whether it was of the look on her face or his mother, she wouldn't know.

"She's stupid if she thinks I'll let her do anything to the two of you." It would've been a little endearing to the elder Winchester if it was any other situation, though he couldn't speak his concerns before she left his lap, and picked up her phone.


End file.
